Hot for Teacher
by PuffPiece
Summary: Dean gets a job (sort of) and gets back on the horse (in a manner of speaking). Eighth in the Reality Bites series – follows Turn the Page. Warnings for amputee Dean and implied Adult Behaviors.
1. Chapter 1

**Disclaimer: The only thing I own are the ridiculous situations in which I've placed these boys.**

A/N: Not sure that this will satisfy those of you wanting Dean to get a job, but I hope those of you looking for Dean to get back into the dating world (Mandy – I'm looking at you) will get some enjoyment out of this one….

Sam didn't really notice anything much at first.

Of course, he's been busy with work, trying to put the finishing touches on a presentation his team's been working on, leaving him little time to pay attention to what his brother's been up to. It's taken most of his concentration just to make it through the day – working until 2 AM most nights, coming home to fall into bed (after making sure Dean's basic needs have been taken care of), only to turn around and do it all over again four to five hours later.

And despite the long hours, tedious tasks, and a few of his more annoying coworkers, he really does enjoy his job.

Loves the mental challenge, loves the stability, loves not having to worry about whether or not he'll need stitches at the end of the day.

So it's not surprising that it takes him a little longer than usual to catch on to the fact that his big brother's up to something.

At first, he'd just thought that perhaps Dean was scamming credit cards again, even though they'd talked about it, both of them agreeing that with their new lives and their permanent address such a thing would be unwise at best, downright stupid at worst.

Not to mention the ensuing awkwardness should Dean get busted. Sam being in the legal profession and all.

But then he begins to take note of the things he's pretty sure are new to their little world. Like the upgraded electric can opener, the previous one having crapped out a couple of weeks ago and Sam not having had the chance to replace it yet. And is that the food processor Dean's mentioned a couple of times?

And that's when he notices the significant increase in his brother's phone activity.

He's pretty sure Laura hates the phone; has heard her say those exact words (plus a few additional colorful curses) in fact on several occasions. And there's no way he can see Kelli's parents letting their six-year old anywhere near a phone, especially given her motor mouth and her penchant for divulging rather sensitive information. And although Dean has been getting out of the apartment more, Sam doesn't think there are that many more people that his brother would actually want to talk to.

So he decides to take matters into his own hands.

Dean's out in the kitchen, trying his best to figure out how to put together the makings for chicken salad (the food processor opening up a world of chopping and mixing that had previously been out of his reach, so to speak, since his injuries), while Sam's reclined on the sofa in their living room reading through the notes of his current project, when he notices Dean's phone begin its incessant buzzing on the coffee table in front of him.

He glances around, craning his neck to catch a glimpse of Dean, still safely in the other room struggling with the jar of mayonnaise.

Fairly certain that his brother won't be winning that particular battle with a screw top lid any time soon, he picks up the phone, swiping across the screen in order to pick up the call, raising the phone to his ear in an attempt to gain some insight into his brother's secretive activities once and for all.

And then quickly regrets his decision.

"Finally," says the breathless female voice from the other end of the line after his tentative "Hello". "Thought you'd never pick up. I've been desperate to talk to you all day. I just can't stop thinking about what you said last night."

Sam's eyebrows creep towards each other as he tries to figure out who's on the other end of the line and what she could possibly be talking about, his jaw dropping and his eyes widening as she rehashes last night's conversation for him in vivid detail.

Very vivid.

By the time she's stopped talking, Sam can practically feel the skin of his face beginning to peel off from the intense flush of his face. He doesn't think there's enough Lysol in the world to disinfect his brain from the mental images the woman has burned into his head.

"Hey Sam?" Dean calls out, mayo jar held between his thighs as he wheels himself back into the living room in order to ask for his brother's help with the stubborn lid that's doing little more than piss him off. "Dude…" he trails off, his initial smirk at the expression on Sam's face quickly changing to one of wide-eyed horror as he hears snippets of the conversation drifting out of the phone that Sam's now holding away from his ear, fingers holding the phone carefully by the edges as if just its touch is enough to make him dirty.

A sentiment echoed by the female voice that continues to drift into the living room, her words of "dirty, dirty, girl" heard equally by the brothers.

"Hello?" comes the disembodied voice, her previous seductive murmurings taking on a more confused tone after her last words failed to garner a response.

Dean lets out a strangled yelp, quickly wheeling himself over to Sam, snagging the phone awkwardly between his stumps as he utters a quick "Can't talk now. Gotta go. Later," before dropping the phone into his lap and jabbing at the display with the end of his right arm in order to end the call.

The brothers stare at each other in frozen silence for a beat of a few moments, each one trying to figure out what to say to the other, Sam finding his voice first.

"Phone sex, Dean? Really?"

The older Winchester shifts uncomfortably in his chair, his glance sliding anywhere but up to meet Sam's eyes.

"Dude," Sam says, his initial tone of disbelief taking on a gentler edge, his big puppy dog eyes softening as he tries to see things from his brother's point of view.

His brother who used to have what one might call a very active social life.

Who used to take delight in working his pent-up energy and frustrations out on the fairer sex.

Who is now confined to a wheelchair, stuck in a body that no longer holds the same power over the female species.

So he guesses it kind of makes sense that Dean would resort to something like this, even though he still can't quite wrap his head around it.

"I know it's been hard, man," Sam says, trying to dispel some of the awkwardness still hanging in the air. "But if you're ready to get back out there, I'm sure there are more than a few women who would be interested. You don't have to pay for phone sex."

Dean gives his brother one of his "what the hell are you talking about" looks before his expression slides from confusion to outrage.

"No way, dude. I'm not the one paying," he says with a vehement shake of his head. "They're paying me."

He's only been doing this for a few weeks; had stumbled into it completely by accident when he'd been visiting some of his less-than-reputable websites. But he's already got a couple of repeat customers. Happy repeat customers.

Because Dean's good.

Really good.

He's always known his way around women, although in the past it's usually been his body and his cocky self-assurance that had been the big draw. But he'd been no slouch in the verbal aspects of his interactions either, more than a few of his endless stream of women telling him what his sexy voice and lurid suggestions did to them.

In fact, Dean's wondered on more than one occasion over the past few weeks why he didn't think of his years ago. It's certainly right up his alley; easier than hustling pool. And much less apt to end in an ass-kicking. Although one of his kinkier clients has asked if he does that as well. It's also kind of helping him think about getting back up on the proverbial horse without the fear of rejection.

And while his body is definitely not up to snuff, he still has his voice and his years of experience.

And even though this doesn't give him anywhere near the same satisfaction as his previous hands-on days, it at least offers him some semblance of being a normal guy.

Something he hasn't been since his run in with the Black Dog.

Not to mention the fact that he kind of likes the satisfaction of knowing that he can help Sam out a little bit, help lift the financial responsibilities just a tad from his overworked little brother. Because even though he knows Sam loves his job and continuously reassures him that they're fine, keeps telling Dean that his job is just to keep getting his life back together, he's still the big brother.

()()()()()()()()

Sam's unusually quiet for the next few days, a sure sign to Dean that his brother's brain is working furiously.

He'd just been hoping it had been occupied with his case at work.

He was wrong.

Because Sam has been busy pulling together a plan that's been loosely floating around in his head since Kelli's party. Something that will get his brother out of the house and hopefully ensconced in some activities a little more socially acceptable than his current gig. Not that he quite thinks Dean's doing anything wrong. In fact, the more he thinks about it, the more Dean's foray into the world of Phone Sex Operator makes total sense.

But he still thinks his brother's selling himself short, has some significant contributions to make to society in general and one little corner of their world in particular, and so he goes about making the necessary phone calls, pulling a couple of strings at work to get the appropriate clearances, and pushing a couple of questionably authorized forms through the proper channels.

The day all of the pieces finally come together, Sam ambles into the living room, having just gotten off of the phone with Tammy, catching Dean as he's trying to get Kelli's socks onto his arms, a low growl of frustration emanating from his throat as the little fuckers outwit him yet again.

"Here," Sam says, holding out his hand in order to help Dean get the socks onto his stumps.

"I can do it," Dean mutters, his face locked in a fierce scowl as he continues to try to use the ends of his arms to tease apart the opening of the socks in order to work them into place.

Sam has no doubt his brother can do it. He's proven time and time again that he can relearn the things that had at first seemed so daunting. It's just a matter of when. And if it'll be while they're still young.

But instead of forcing the issue, Sam just plops himself down on the sofa, trying to discretely keep an eye on his brother's progress even as he thumbs through the pages of one of the books Dean's been reading to Kelli.

"So, Tammy mentioned that Kelli's class is looking for some helpers," Sam says, doing his best to sound nonchalant.

"Yeah?" Dean replies, his focus still on the limp pieces of cloth in his lap. "You thinking about volunteering?"

Sam barely contains the snort Dean's question triggers. Because there's no way in hell he has any desire to be that close to so many six-year olds. Especially ones that call him a smelly Sasquatch.

Sam shakes his head when Dean finally hazards a glance his way, shifting uncomfortably on the couch, all of the sudden having second thoughts about putting this together without Dean's input.

"Uhhhh, no."

Dean spares him another glance before giving his brother an eyeroll. "Out with it Sam. I know there's something rattling around in that pea brain of yours. Spill it."

"So I was thinking," Sam begins, which triggers a groan from Dean who's all too well aware of his brother's predilection for putting his thoughts into action. And that action is usually about him. And it's usually an action he'd rather avoid.

Like the first time Sam had decided that Dean was ready to go with him to the grocery store. It had gone okay until Dean's wheelchair had accidentally clipped the display of Campbell's soup, sending errant cans cream of tomato tumbling to the floor in a cacophony of clatter. Needless to say, Dean's been avoiding that store since. And Sam still can't look at tomato soup without cringing.

But a lot of Dean's moaning and groaning is all for show. Because he knows Sam really does have his best interest at heart. Even if he is a little weasel about it sometimes.

And he has to admit that although the idea Sam's detailing does kind of strike fear into his heart, it's actually kind of intriguing.

Because Sam's arranged to have Mister Dean read to Kelli's morning Kindergarten class once a week, maybe more if the initial couple of times go well.

He'd initially spit-balled the idea with Tammy at Kelli's birthday party, speaking with a few of the other parents before they'd left, trying to gauge their interest and comfort level with his brother.

And when he'd followed up with Tammy a few weeks later, she'd let him know that the kids in Kelli's class hadn't stopped talking about the birthday party for days, practically driving their respective parents crazy with requests for more Reading Time with Mister Dean.

So it had seemed like something that would be a sure win-win, assuming Dean agrees.

And of course Dean caves, after the requisite grumbling and expressions of disgust and disbelief over Sam's underhanded behavior, finally offering his begrudging agreement to join the class as their designated reader this coming week.

Because he's Dean Winchester.

And that's just the kind of guy he is.

 _ **To Be Continued…**_

A/N 2: Please drop me a line and let me know if you're continuing to enjoy this series. Feedback craved and ideas for future stories welcomed!


	2. Chapter 2

**Disclaimer: The only thing I own are the ridiculous situations in which I've placed these boys.**

A/N: A heartfelt Thank You to all of you Reviewers – your continued words of interest and encouragement with this series help to power the wheels of my devious little brain.

"You need any help with anything?"

"No, I'm okay. Thanks."

Dean's gotten used to this frequent exchange. And where it used to leave him screaming internally, railing against the unfairness of it all, he now just takes it in stride. Especially when it comes from someone within their little circle.

He's currently sitting in his wheelchair, plotting out his necessary steps in order to transfer himself into Tammy's car without taking a spill. Because it's his first day of school, as Sam's been oh-so-helpfully calling it. And he'd rather not start it in a heap on the ground.

Tammy had arranged to act as a classroom helper for the morning, she and Sam conferring together and determining that her presence would help somewhat to put Dean at ease, giving him another friendly face in a sea of uncertainty. And since Sam has to work, she'd also offered to act as chauffer for the elder Winchester as well, which is a bonus, seeing as how he hasn't yet tackled public transportation.

"You mind getting the door for me? Chair too?" he asks on second thought once he's managed to transfer himself into the passenger's seat. They've made some adjustments to the Impala allowing Dean to perform some of the more mundane activities, the cloth loops tied to the door handle at least allowing him to pull the door closed, but Tammy's car has no such adaptations, so rather than just sit there and wait for her to figure it out on her own, he's learned to go ahead and say what he needs help with.

Even though there's still a part of him that hates it.

"Oh, yeah. No problem," she says, hustling back around to the passenger's side and following his instructions on how to get his chair collapsed and stowed in the back seat.

"Alright, you ready?" she asks, sliding a glance his way, making sure his seat belt is in place prior to pulling out of the parking lot of their apartment building.

"Sure," he says, his reassurance losing some of its effectiveness by the uncertainty in his voice.

"Oh come, on," she says rolling her eyes at him. "You'll be great. You know the kids will love it. No sweat."

Yeah, easy for her to say. She's not the one heading into an unknown situation without a way to make a break for it if things go south. Not that he thinks they will. But still, it'd be nice to have some options. Besides rolling himself the ten miles back home, dodging traffic and the stares of curious passersby.

Sometimes he really hates his life.

()()()()()()()()

"This way," Tammy says, directing Dean towards the administration suite where the sign clearly reads "All Visitors Must Sign In", a stark reminder to Dean of just how much the world has changed since he and Sam were kids, when unknown visitors didn't trigger nervous glances and the Spanish Inquisition.

"Sign in," echoes the disinterested woman behind the front desk in a raspy voice that hints at decades of smoke inhalation, barely sparing the two of them a glance over her half-glasses before shoving the clipboard in their direction.

Tammy follows orders, then bounces her glance between the clipboard and Dean, an "Uhhhhh," escaping her lips as she tries to figure out her next move.

"I got it," says Dean, wheeling himself so that his chair butts up right against the desk, adjusting his position to get himself as close as he can. "Can you maybe just hold the clipboard steady for me?" he asks, working to get the pen trapped between his stumps before painstakingly adding his name to the list of visitors on the school's campus.

And while it really looks like "Dean Winchester" is a visiting second-grader at best, if the block letters of his signature are anything to go by, the mere fact that he can actually manage to sign his name in any capacity is a miracle in and of itself, a testament to the endless hours of practice he's been putting into the otherwise mundane task.

Because in addition to the hours he's spent reading with Kelli, he's been practicing writing with her too.

They've been spending a fair amount of time working together, Kelli trying to remember how many humps the "M" has compared to the "N" and how many arms the "E" has compared to the "F", while Dean tries to figure out the logistics of making his name legible with the arms he himself actually still has left.

The woman behind the desk glances at their names, spares Dean a second more thorough look, and then quickly taps away at her computer, giving a brief nod of satisfaction upon seeing both of their names and the appropriate paperwork already catalogued in her system.

"Alright," she says, sliding a pair of "Visitors" badges across at them, "bring these back before you leave."

Tammy swipes both of the badges off of the desk, leading Dean down the main hallway towards Kelli's classroom and well out of earshot before murmuring under her breath, "It's a good thing she's got such a sparkling personality", causing Dean to let out a huff of a laugh in return.

"Alright, showtime," Dean murmurs to himself when they arrive at Kelli's classroom, giving a quick nod to Tammy after she's knocked on the door, the muffled "Come in!" followed by the teacher's next words, clearer now that he and Tammy have made their way inside.

"Class, we have a special visitor today for reading time."

"Mister Dean!"

Kelli's shout of excitement heralds a few other calls of "Hi Mister Dean", as well as a few murmured "Where's Sasquatch?" comments from the class, the poor teacher trying desperately to prevent chaos from breaking out at the arrival of their visitors.

Dean casts a glance at the woman, his anxiety level kicking up yet another notch when he gets a good look at Kelli's teacher.

Because she's definitely someone Dean would have put the moves on back in his former life.

Cute blonde, wide innocent doe eyes, soft hair curling gently around her face.

Crap. As if he needed something else to feel insecure about.

"Miss Christie! Miss Christie!" Kelli says, addressing her teacher, practically bouncing in her seat, eyes wide with excitement. "This is my friend Mister Dean!"

"Yes, I know," the teacher says, kneeling down next to the girl's seat, throwing a bemused smile towards Tammy and Dean. "He's here to read for us today. Is that okay?"

Kelli's nod of enthusiasm is echoed by several of her classmates, bodies scrambling towards the designated Reading Rug in anticipation of their daily story session.

"Hey Kiddo," he says quietly to Kelli as she walks with him over to the edge of the rug, "can you help me out?"

Kelli nods eagerly, taking the socks from Dean's arms when he offers them to her, allowing her to work them up onto his stumps before making some final adjustments to their positioning on his own. It's been getting easier for him to get them on, but he'd decided to just bite the bullet and ask for Kelli's help, figuring she'd jump at the chance to help with her gifts while also figuring nobody really wanted to sit around and watch him struggle with them for another half an hour.

Once he's settled into his designated reading area, Kelli nestled on his lap to help him hold the book, he can feel his anxiety levels start to slip away, his focus shifting from his questions and self-doubt to making sure his character voices keep the kids engaged.

So when he reaches the end of the story, it's a toss-up whether he himself or the kids are more disappointed. Because he really does enjoy it. Loves seeing the look of joy on the kids' faces. Loves being able to just leave his life behind and take a trip to a happier place. And he even takes a bit of satisfaction at seeing the look on the face of Miss Christie, because he doesn't think he's imagining the spark of interest in her eye either.

But he's nowhere near ready to make a pass at a perfect stranger, not yet anyway. And so he bides his time until Tammy's ready to leave, chatting with the kids about their book preferences, what they're currently learning, and how much shampoo it takes to wash a Sasquatch, returning the smile and wave the teacher sends him on his departure with a tenuous smile of his own.

And as he rolls himself back down the hall, Tammy at his side as they brace themselves for another interaction with Ms. Sparkling Personality, he thinks that sometimes his life doesn't suck so much after all.

()()()()()()()()

"So how was school?" Sam drawls, a teasing edge to his voice even as he genuinely inquires about Dean's day.

The brothers and Laura are seated around a table at a local Italian restaurant, celebrating the fact that Sam's presentation has finally wrapped up, affording the younger Winchester a slightly lighter workload for the foreseeable future, not to mention a more routine meal schedule.

So he'd rallied the troops, gathered them together for dinner in an attempt to catch up with the things he's missed out on over the past few hectic weeks.

The fact that it will also afford him the chance to tease Dean about his first day school is an added bonus.

"It was his first day of Kindergarten," Sam adds for Laura's benefit. "They grow up so fast," he says in an overly dramatic weepy voice, wiping an imaginary tear from the corner of his eye.

"Shaddup," Dean says with an eyeroll and an exasperated shake of his head, turning his attention back to the breadsticks the waitress had brought after taking their orders, carefully spearing one of the soft chewy appetizers with his adaptive fork.

"You gonna fill me in here or what?" Laura asks around a mouthful of her own breadstick, glancing between the brothers as she tries to figure out what the hell they're talking about.

"Genius over here decided that I needed to get out of the house more," Dean says, giving his brother a stare that makes it very clear to Sam that he's not to divulge the "why" behind his actions. "Signed me up to be a volunteer reader in Kelli's class."

"Kelli?" Laura asks, eyebrows furrowed as she tries to place the name.

"Oh yeah," Sam interjects. "I don't think you've met her yet. Dean's bestest friend," he adds, reiterating Kelli's words with a flutter of his eyelashes.

"Oh right," Laura says, nodding now that she recalls the boys having mentioned Dean's little friend on more than one occasion.

"So," Sam says again, still trying to find out the answer to his initial question. "How was it?"

"Not bad," Dean admits as he chews on his breadstick. "It was probably the best one I can remember," he adds, his mind taking quick stock of just how many First Days he and Sam have actually had, easily triple the average child's amount given how much they'd moved around.

"Wait," Sam says, "what about that one time you managed to start a fist fight between those two cheerleaders."

"Oh yeah," Dean says, a rather smug smile creeping onto his face as he recalls that day. "That was awesome. Hair pulling. Hand slap fighting. A lot of name calling." Each had been so eager to be the first to make the acquaintance of the New Guy that it had ended in fisticuffs in the parking lot after the final bell had rung. Not being one to take sides, he'd made sure to make both of their acquaintances. On numerous occasions.

Sam doesn't miss the wistful look that crosses his brother's face an instant later, nor does he miss the slight flush that creeps up his neck as he shifts in his chair, giving a slight nod to a young woman who's entered the restaurant at the tail end of a small group of young-professional type people.

"Hey," she says to Dean as she passes by their table. "Great job today. The kids really loved it."

"Thanks," Dean says, his eyes trailing after her as she follows her companions to a booth at the other side of the restaurant.

"Dude," Sam whisper-hisses at him, shifting himself around in his seat in an effort to surreptitiously check her out. "Who was that?"

"Kelli's teacher," Dean says, trying to keep his voice carefully neutral. Because, yeah, she's right up Dean's alley. And he's pretty sure Sam's going to know.

"Oh, she's cute," Laura says, nodding in approval. "No ring either," she adds, having contorted herself rather conspicuously in order to get a good view of her left hand. "You should make a move."

Dean lets out a groan, knowing that he's well and truly sunk if Sam and Laura decide to join forces and gang up on him.

"Seriously," Sam adds. "You thinking about making a move? You hot for teacher?" Sam asks, a slow grin sliding across his face as he waggles his eyebrows at his brother, enjoying making his brother squirm.

"Shut up."

Dean's given a brief reprieve when their foods arrives, his plate of baked ziti offering him a diversion as he turns his attention to cajoling the individual pieces of pasta onto his fork and into his mouth without having them take any unnecessary detours to his lap or the floor.

Sam and Laura, however, need no such concentration to get the food into their mouths, giving them the opportunity to continue to offer unwarranted encouragement in a realm of his life he's not quite sure he's ready to tackle.

"Oh come on," Sam says, his tone that of extreme exasperation after Dean's continued to voice his protestations in regards to making any sort of advances. "You're a Phone Sex Operator for Pete's sake. I'm pretty sure you can handle this."

"Eeehhh," Dean says in a strangled tangle of vowels, giving Sam an imploring look in order to get him to shut the hell up and keep his voice down.

"Wait, what?" Laura asks, leaning forwards in interest. "Phone sex? When did this happen?"

"Would you guys shut up?" Dean hiss-whispers, distributing his Death Glare equally amongst his table mates while glancing around to make sure no one's been privy to their conversation.

"You any good?" Laura presses, her spiked eyebrow raised to the ceiling as she takes a sip of her wine.

"Oh my god," Dean mumbles, wishing he still had hands just so he could palm his face in exasperation.

"That's what she said," Sam chirps, clearly enjoying making his brother squirm.

Laura gets a rather wicked look in her eye and raises her glass in a mock salute. "Dean Winchester. Kindergarten volunteer by day. Phone Sex Operator by night."

"Now that's classy," adds Sam, raising his own glass and clinking it with hers.

Yep. Dean Winchester, ladies and gentlemen. A real class act.

 _ **To Be Continued…**_


	3. Chapter 3

**Disclaimer: The only thing I own are the ridiculous situations in which I've placed these boys.**

"That's a really good look on you Sam," Laura says as she follows Dean into the living room of the brother's apartment.

Sam just rolls his eyes at her, shooting his brother a Bitch Face for good measure as well.

Because he's currently seated on the floor, Kelli perched above him on the couch, scrolling through his computer while she guides his hair into something that would make the front man for A Flock of Seagulls jealous.

Dean just snickers, providing introductions of "Laura, Kelli; Kelli, Laura" before the older of the two females continues into their kitchen on a quest for a cup of coffee that won't make her consider quitting her most favored addiction, the lingering taste of her aunt's freeze-dried decaf still making her nose wrinkle in disgust.

"What's that?" Kelli asks, glancing up from Sam's head with interest when Laura joins them back in the living room, letting out a low moan with her first sip of delicious hot java.

"Liquid heaven," Laura replies, quickly taking another sip from the mug cemented in her hands.

"Can I have some?"

"Oh dear God, no," Dean's quick to reply, throwing Sam a panicked look at the thought of the already rambunctious six year-old on caffeine. It'd be like giving her liquid speed. "Come on," he adds, seeing the disappointment on her face, "let's see if Sasquatch got us anything good for a snack."

He shoots Sam a look that's a mixture of relief at having headed the potential caffeine disaster off at the pass and a smirk at both his brother's ridiculous hairstyle and his continued pet name for Sam.

Sam is not amused on either front.

But the younger Winchester seems to have gotten over his brother's ribbing by the time Dean and Kelli return from their exploration of the kitchen, his face now much more relaxed, a smile playing along the edges of his lips as he and Laura share a couple of glances.

Which immediately puts Dean on edge.

"So Kelli," Sam asks, using his fake innocent tone that Dean knows only too well. The one that makes him think his little brother's up to something.

As well it should.

"You like having Mister Dean come to your class to read?"

Kelli nods enthusiastically, her pigtails bobbing furiously even as she sips on the one No Sugar Added juice box she's allowed to have as a treat when visiting with Mister Dean. God help them when she gets ahold of a second one. They'd practically had to peel her off the ceiling.

"You think your teacher likes it when Mister Dean comes to read to the class?"

"Uh huh," she says, again nodding her head in affirmation. "Cause then she gets a minute to herself," she says, parroting her teacher.

"What's your teacher's name again?" Sam presses, knowing full well her name from having talked with Tammy while setting up this whole ordeal.

"Miss Christie."

"Is there a Mister Christie?" Sam asks innocently, even as he catches Dean's eyes narrowing as the elder Winchester gets the gist of where this conversation is headed.

"Nope!" Kelli chirps. "She tells us we give her enough trouble as it is."

Sam loses the fight to keep his dimples in check while Laura practically chokes on the coffee that's taken a wrong turn in her throat.

"She sure is pretty," Sam continues, bouncing his gaze between his squirming brother and the little girl who's looking rather pleased to have so many answers to Sam's questions. "Do you think she's pretty?"

Kelli again nods her head eagerly in agreement.

"Do you think she's pretty?" Laura pipes in, directing her question to Dean, doing her best to look innocent.

Dean shoots the two of them a look that's the verbal equivalent of a "fuck you", hazarding a glance towards Kelli whose attention is fully on him, awaiting his response to Laura's question, a sinking sensation taking root in his gut.

Because he knows that he is well and truly screwed if Sam and Laura manage to get Kelli in on their little game plan.

He would do pretty much anything for the little girl who's been instrumental in helping him relearn who he is. Helping him to not quite feel so awkward in his own body. Getting him more comfortable with figuring out new ways to do old things. Reminding him of who he is deep down in his core.

And Sam knows this.

Dammit. His little brother really is a sneaky sonofabitch.

()()()()()()()()

"Well hello there," Dean drawls in the low throaty voice he uses when he's talking with a potential new phone client for the first time.

He's figured out that while he's in the business of giving a form of pleasure to these women who call, it is, after all, just a business. Just a way to score a few quick bucks. And part of his business is trying to figure out what his customer is really looking for, who it is she wants him to be. So until he gets to that point, he uses the same persona he's used countless times over the years, the one that was accompanied by his cocky swagger and his killer smile.

The one that practically had the women melting on the floor.

A guy he's not sure even exists anymore.

He's in the midst of his typical spiel with his newest client, midway through the part where he describes what he's wearing (or not), carefully detailing the way he's slowly unbuttoning his shirt, when a familiar peal of laughter from the other end of the phone brings him to a sudden halt.

"Laura?"

"Oh my God," she pants in between her continued hoots of laughter. "Are there suckers out there who really fall for this?"

"What the hell?" he growls, glaring down at his phone. "Did Sam put you up to this? How'd he even get this number anyway?"

"Oh relax," she says, still hiccupping between her gasping breaths. "I just decided to see what all the fuss was about. Sam's not the only one who can find an unlisted phone number, you know. So this is how you're spending your evenings now, huh? Hustling these poor deluded women out of their hard-earned money?"

"Hey," he says, "they're calling me. I'm not holding a gun to their heads. And besides," he adds, a hint of his smug smile evident in his voice, "they are not going away disappointed."

"Pfffhht," she says in disbelief. "De-lu-ded," she repeats, enunciating the syllables in an effort to add additional weight to her comment.

Dean narrows his eyes, mentally running through his repertoire, a lascivious smile sliding across his face as he alights on something he knows is money in the bank.

Because nobody's ever walked away from Dean Winchester with a complaint.

Several minutes later and Laura's "Oh my God," has a much different tone. "You really are good."

He's better than good. He's Dean Winchester. And he's great.

()()()()()()()()

Dean really can't believe he let Sam talk him into this.

Well, yes he can. Especially given the fact that it was not only his conniving little brother, but his sidekicks Laura and Kelli as well, who have somehow managed to manipulate him into playing right into their weasely little hands.

And so now he sits at a table in the little coffee shop down the street from their apartment, a cup of untouched coffee in front of him, waiting for Miss Christie to arrive.

And trying valiantly not to freak the fuck out.

Because while Sam's made it clear that he thinks Dean should be able to handle going out with a woman no problem, given his side job, Dean knows that the two are vastly different.

That on the phone, he's just some faceless voice, giving his client what she wants to hear. That there's no strings attached, no risk of rejection (other than an unsatisfied customer lodging a complaint and refusing to pay), no emotional involvement.

It's not real.

Unlike the very real panic that's threatening to send him hauling ass back to the safety of their apartment in a quivering ball of shame.

Because as much as Sam has tried to allay his fears, his heart's still beating way too fast, his throat's still way too dry, and his palms (if he still had them) would be way too damp.

"Come on man, snap out of it," he mutters under his breath, trying to channel one of his brother's recent exasperated pep talks in an effort to break the endless loop of self-doubt that's circling his brain even as his arms stumps make a few rapid trips against his thighs in an effort to dispel some of his nervous energy.

He takes a couple of slow, deep breaths, giving one last audible gulping swallow when he catches sight of Kelli's teacher heading his direction, then puts on one of the bravest smiles he can muster.

 _Oh shit._

()()()()()()()()

By the time Dean feels his phone vibrating under his leg, the signal he'd arranged with Sam in order to provide the necessary "out" should things go horribly awry, he merely pokes at the screen in order to hang up the call, effectively letting Sam know that he doesn't need him.

That he's doing okay.

Because he is.

In, fact, he's doing more than okay. He's actually enjoying himself.

As is Christie, if Dean's reading her body language correctly – the twirling of her hair, the way she's leaning into the table, the shy smile and lingering eye contact she keeps sending his way.

And all of a sudden, Dean's anxiety is back in a "Holy Crap" moment as he considers the possibility that there might actually be women who still find him desirable. Who might want to do a little more than just have coffee. And talk.

Because he doesn't even have all of the necessary equipment to give himself a proper hand job, for fuck's sake. What the hell is he going to do if he finally does manage to get lucky?

"You okay over there?" Christie asks, concern clouding her face as she takes in Dean's expression, his laughter having devolved rather quickly into a panicked wide-eyed stare that's beginning to make her question if she's committed some sort of heinous faux pas.

"What?" Dean asks in a strangled voice, shifting in his seat uncomfortably. "Yeah, fine. I just think I forgot something," he says with a weak smile. _Yeah, like my balls,_ he thinks to himself, swallowing convulsively against the constriction in his throat.

"Oh, okay," Christie says, uncertainty in her voice as she tries to figure out just where things went wrong. She'd thought they'd been having a good time, both of them relaxing after the initial few minutes of uptight small talk once they'd gotten started trading stories about Kelli and her classmates.

And while at first she'd been more than a little hesitant to meet up like this, in part because of her natural shyness around the opposite sex and in part because of his rather significant disability, her heartstrings had been tugged just enough by an unrelenting Kelli, her not-so-innocent comments of "Mister Dean thinks you're pretty" and "I think you and Mister Dean should play together" too cute (and persistent) to ignore.

So when Kelli had practically cornered the two of them together after one of Mister Dean's reading sessions and asked each of them if the other would like to meet for coffee, neither of them had refused, unwilling to submit themselves to further nattering by Kelli or wanting to cause embarrassment to the other.

And she likes Dean, she really does. He's great with the kids, seems to have a wonderful connection with Kelli; she knows kids are a great judge of character. And the more she's talked with him, the more she's able to see past the wheelchair. She's still not quite sure yet if she'd accept a request for another "playdate" as Kelli had called it, but she's considering it more than she had been an hour ago.

At least until Dean makes his next move, virtually quashing any further thoughts in that direction.

"I'm sorry," he says, the hint of a tremor just barely detectable in his voice, the wild-eyed panic still quite evident on his face. "I've just…. I've got to go."

And with that statement, he wheels himself away from the table, nodding a hasty goodbye to the baristas on duty, before heading back to his apartment, second-guessing himself all the way.

Because seriously? What the hell had he been thinking?

 _ **To Be Continued…**_


	4. Chapter 4

**Disclaimer: The only thing I own are the ridiculous situations in which I've placed these boys.**

"Dude. You didn't."

"Yeah, I did," Dean says, not even bothering to stop and look at Sam as he rolls himself towards his bedroom. "Look man, don't start. I'm not proud of it. But at least I went, right?"

"Yeah, but you just left her there. By herself."

"I know," Dean says, pulling his arms off of his wheels before he reaches his room, his head dropping against his chest as he heaves out a weary sigh. "It's just…. I just couldn't…." he stammers, turning his chair to face his brother, throwing Sam a beseeching glance only to get a Bitch Face in return.

"Good thing you're scheduled to go back to Kelli's classroom tomorrow," Sam says, shaking his head in disbelief.

"And how exactly is that a good thing?"

"Because you can apologize," Sam replies, the "duh" quite evident in his tone of voice.

"Apologize?" Dean asks with an incredulous raise of his eyebrows. "If anyone should be apologizing it's you. Don't think I'm not wise to you and Laura using Kelli to gang up on us like that. Pulling her Little Miss Innocent act."

"Well then, fine. I'm sorry," Sam says, his tone of voice, not to mention its volume, saying the complete opposite. "I'm sorry that I want to see you happy. I'm sorry that I want to see you get back out there."

"Sammy," Dean says, jumping in when his little brother pauses. "I get it. Really. I do. You think that since I'm doing the whole Phone Sex thing I should be able to move on. That I'm ready to put my moves on the ladies. But it's not the same man. On the phone I can be whoever I want - figure out what they want and give it to them. I don't have to be me."

"But you're great, Dean. Why wouldn't you want to be you?"

"Uh, have you seen me?" Dean asks rhetorically, sweeping his right arm over his body. "Not too much left to brag about." He sighs again, worrying his lower lip as he weighs his next words. "Sam. I've been a chick magnet since junior high. They love me. Or they did. But I just don't know anymore. I don't know if I have anything left that they'd want."

Sam sits down rather heavily on their sofa, completely floored by his brother's rather honest admissions. Because trying to get a read on his brother sometimes is akin to trying to find something that rhymes with 'orange'. Although since the Black Dog, Sam has to admit that Dean has been opening up a bit more. Probably out of sheer necessity, but whatever. So he weighs his words carefully, aiming for the right amount of honesty and humor that usually gets through to his brother.

"Dude. Come on. I know you don't really believe all of that. And anyways, you've got plenty of what women are looking for. You're charming. You're funny. Well, I don't think you're charming or funny, but they do," Sam hastily adds, garnering an eyeroll of response from his brother. "And come on. You're still you. Still Dean Winchester. The guy any woman would be lucky to be with."

Dean gives Sam a considering look, rolling himself back and forth slightly as he ponders his brother's words.

Because some part of him might still believe the contents of Sam's pep talk; it's the parts of him that the Black Dog ripped to shreds that give him serious pause.

()()()()()()()()

"So you totally screwed the pooch, huh?" Laura says as she packs his chair into her backseat. She's playing designated driver for the morning, having no client meetings and a couple of holes in her schedule, not to mention wanting to get a first-hand account of Dean's Big Evening.

Dean just rolls his eyes and lets out a disgusted sigh, laying his head back against her headrest, having no energy left for further self-defense.

"Well, I guess you just get down on your knees or whatever," she says, with a vague wave of her hand towards the remainder of his legs, "and beg for forgiveness."

"Seriously?"

"Dude," she says, giving an exasperated huff/eye roll/head shake combination that she'd used on her brother on more than one occasion when he was being a total idiot. "You left a girl. By herself. On a first date."

"I know," Dean groans, having berated himself similarly for the entirety of his previous sleepless night.

Because that's not him.

Sure, he's had his fair share of One Night Stands (and Sam's too, and probably several other peoples' if he's counting), but he's never done something douchey like he did to Christie.

Of course, he's never had this much self-doubt, either.

But he knows that Sam and Laura are right, just as he knows that he's got to try to explain himself to Christie.

And as much as he hates Chick Flick Moments, he kind of hopes that there's one waiting for him right around the corner.

()()()()()()()()

Dean takes a couple of deep, calming breaths, slowly blowing them out in an effort to get his nerves under control, briefly considers turning tail and getting as far away from Kelli's classroom as is humanly possible, then decides to suck it up and deal.

Because either Sam or Laura, or quite possibly both, would more than likely hunt his crippled ass down and drag him kicking (or whatever the equivalent of what his leg stumps can do) and screaming back to Kelli's school in order to apologize to Christie once and for all.

Heart threatening to pound out of his chest, he knocks on the door with his elbow, waiting for what seems like forever until the door is opened by the designated Classroom Helper for the day, a little boy named Todd who gives Mister Dean a bright smile and a cheerful "Hiya".

Dean scans the room after giving Todd a brief greeting in return, his eyes alighting on Christie sitting at her desk at the front of the room, sparing him a quick tight smile before turning her attention back to the room.

"Okay class, Mister Dean's arrived. Let's make our way back to the Reading Rug. Quietly," she adds in vain as the deluge of little bodies descends on the corner designated for story time.

Dean's story, while full of intrigue (well, as full of intrigue as a story about a hungry caterpillar can be, anyway), is lacking in its usual pizazz, his mind otherwise occupied by the other adult in the room, a decidedly aloof Christie who's doing her best to avoid unnecessary eye contact and stay as far away from him as she possibly can.

She's made sure to keep at least child near her at all times, a pint-sized human shield to keep her emotions from coming under further fire as she tries to ride out the humiliation of having to come face-to-face with her deserter yet again.

So it takes some creative thinking (and maneuvering) for Dean to finally catch Christie by herself, practically sending her through the roof when he heads her off as she's on her way back to her classroom after having dropped off her charges for their weekly field trip to the library.

"Look, I suck. I know. Just hear me out," he says, searching her face for any kind of chink in her armor. And while her stony face isn't exactly what he'd been hoping form, the fact that she hasn't tried to make a break for it yet gives him a seed of hope, which is something he can work with.

"It's just….. I really haven't been out. With a woman. Since this," Dean says, glancing down at his body before darting his eyes back up to hers.

"Oh. _Oh_ ," she says again, her eyes widening at the implication. "Sorry. I mean, not sorry. Well yeah, sorry. About that," she says, waving a hand in his general direction. "Obviously. You know what I mean."

Dean gives a little smile, nodding slightly to show that he understands her perfectly, unable to miss the flush of embarrassment blossoming on her cheeks. "And I guess I just got a little anxious," he continues, giving a derisive snort to his massive understatement. "Okay, a lot anxious. Kind of thought I might pass out right there in the middle of the coffee shop. So I left."

"Oh," she says again, the word breathed out with more relief than she'd been meaning to impart. "Well, why didn't you just say something?" she asks, her eyebrows furrowed in consternation.

"Yeah," he says with a little huff of a laugh, scrubbing the back of his head with his right arm stump. "So I've never really been good with all of that emotional crap. That's more Sam's gig," he says, offering her a wry smile. "And I don't know, I just, I got overwhelmed, got to thinking about stuff. Freaked out."

He wheels himself back and forth slightly, doing his best to pace out his nervous energy, then finally stops, taking a deep breath and letting it out slowly.

"So do you maybe wanna try it again sometime? Coffee? Or maybe dinner? If I promise not to be such a spaz?"

Dean waits, keeping his arms rooted to the wheels of his chair so they don't seek out his thighs in a show of nerves, the pressure in his chest building as he waits for her response.

"Yeah," she says after a few more moments of contemplation, the corner of her mouth twitching upwards in the hint of smile. "I think I would."

()()()()()()()()

As if conquering his inner demons wasn't enough, Dean also manages to crack a rather tough nut he's been working on by the time he leaves Kelli's school for the day.

Because Dean's always been able to win people over. Or piss them off. Sometimes both. It's part of his innate charm that if he flips the proper switches he can usually get people to warm up to him.

And when he'd figured out that the gig with Kelli's class would be going on for a little while, he'd decided that Ms. Sparkling Personality needed a little work.

So he'd set his mind to charming the pants (usually polyester) off of her, laying it on so thick that she'd practically had to scrape it off with a knife by the time he was done signing in and/or out for the day.

And his efforts had paid off. He'd considered it no small miracle when he'd finally gotten a hint of a smile, a raspy "See you next time Doll" his parting sendoff after a few weeks of diligent hard work.

Unfortunately, he would soon regret those efforts.

In fact, he would regret it later that very week.

It's as he's wrapping up his session with one of his bawdier clients, trading sexually-infused barbs with her, that his blood runs cold, even as his testicles creep up into his abdomen for safe keeping.

Because he suddenly recognizes the voice, the words "Next time Doll" eerily reminiscent of a few days back when he'd been leaving Kelli's school on a high.

And it's then that he realizes that his 8:30 Thursday is Ms. Sparkling Personality.

Several seconds later, Dean seriously considers a career change.

 _ **The End**_

 **A/N:** Hope those of you still reading the Reality Bites series found this enjoyable – thanks for your continued support!


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